Drake has never been shy about his love for gambling, and now he’s revealing his biggest win yet. In a promo video for Stake, the betting platform he endorses, the rap superstar shared details about his most memorable victory.
When asked about his largest win, Drake laughed, jokingly calling it a “tax question.” He then recalled a wild night at Dave & Buster’s that led to an unbelievable payout. “I was getting this random girl to call roulette numbers, and I hit, like, eight out of 10 numbers,” he said. “By the end of the night, we had won like $38 million, $40 million. Yeah, $40 million.” He described it as “the craziest night ever gambling,” adding, “January of 2024 was crazy. There’s not even a word for it.”
Drake also revealed an intense betting session with NBA legend Michael Jordan, whom he called his “gambling G.O.A.T.” The two faced off in ping pong during All-Star Weekend in Toronto, and MJ wasn’t willing to accept defeat easily. “He just wouldn’t leave the ping pong table,” Drake said. “He kept betting bands. Like, 10 bands, 20 bands. He kept betting ’cause he just couldn’t stomach the loss.” Despite the high stakes, Drake admired Jordan’s competitive nature, saying, “He’s definitely not a quitter.”
While the 6 God has seen major wins, he’s also taken some big losses. Last year, he placed a $355,000 bet on Mike Tyson to beat Jake Paul, only to watch Tyson lose by unanimous decision. He also lost $2 million in 2022 after backing Israel Adesanya against Alex Pereira in a UFC bout.
Win or lose, Drake clearly enjoys the thrill of high-stakes gambling and he’s got the bankroll to keep playing.
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